For coming out at the turn of the millennium, this show is extremely meta and is somehow timeless while also being very of the year 2000.
The Truman Show style show-within-a-show format is taken and applied to a soap opera as creator Darren Star sends up his own experiences working on 90's teen dramas Beverly Hills 90210 and Melrose Place.
The best part is all episodes are available for viewing on YouTube.
Guest: Jack Moody from The Neighbors Upstairs